Potassium Carbonate → HCID 22391279, compound

HRID 1423406Notes

Reaction equation

HRID 1423406 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].C([O-])([O-])=O.[K+].[K+].Br[CH2:18][CH:19]1[CH2:21][CH2:20]1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:18][CH:19]1[CH2:21][CH2:20]1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 763083-Bromo-4-hydroxybenzaldehydeHCID 81503Bromomethylcyclopropane

Product 1

HCID 22391279HCID 22391279, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A well stirred mixture of commercially available 3-bromo-4-hydroxy-benzaldehyde (40.2 g; 220 mmol), anhydrous K2CO3 (30.4 g; 220 mmol) and commercially available bromomethyl-cyclopropane (32.4 g; 240 mmol) in dry DMF (200 mL) is heated to 60° C. over night. The reaction mixture is filtered, concentrated under reduced pressure, diluted with water and extracted with tert. BuOMe. The combined organic extracts are washed with brine, dried over Mg2SO4 and concentrated under reduced pressure. The residue is chomatographed on silica gel (cyclohexane/AcOEt 100:0 to 85:15) to yield 47.5 g of the title compound as pale yellow oil.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated under reduced pressure
  3. additiondiluted with water
  4. extractionextracted with tert
  5. washThe combined organic extracts are washed with brine
  6. dry with materialdried over Mg2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7021ac9fc98a49509d63e59b78a3b935
Source dataset
uspto-grants-2015_01
Patent number
US08927557B2

Reaction notes

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